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Method for producing silane compound having sulfonyl bond

a technology of sulfonyl bond and silane compound, which is applied in the direction of silicon organic compounds, organic chemistry, chemistry apparatus and processes, etc., can solve the problems of affecting the reflection of active light from the semiconductor substrate, and achieve the suppression of the production of byproducts and side reactions, and the effect of convenient and inexpensive production

Inactive Publication Date: 2017-09-19
NISSAN CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention provides a method for efficiently producing a silane compound with a sulfonyl bond, which is useful as a raw material for a resist underlayer film. The method involves reacting a chlorosulfonyl compound with sodium sulfite in water to produce a sulfinic acid sodium salt, adding an aromatic hydrocarbon solvent to carry out azeotropic dehydration, and adding an aprotic polar solvent and a chloroalkylsilane compound to cause a reaction. This method suppresses production of byproducts and side reactions, resulting in a target compound with relatively high purity. The hydrolyzable organosilane compound produced by this method has specific examples of various substituents and can be used in various applications.

Problems solved by technology

For this reason, influence of reflection of active light from the semiconductor substrate is a sever problem.

Method used

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  • Method for producing silane compound having sulfonyl bond
  • Method for producing silane compound having sulfonyl bond
  • Method for producing silane compound having sulfonyl bond

Examples

Experimental program
Comparison scheme
Effect test

example 1

Production of Compound 1

[0062]

[0063]32.2 g (0.156 mol) of 4-methoxybenzene-1-sulfonyl chloride, 19.6 g (0.156 mol) of sodium sulfite, 39.3 g (0.467 mol) of sodium bicarbonate, and 100 g of water were placed in a 500-mL recovery flask, and heated to 100° C., and a reaction was caused for 1 hour. Subsequently, 100 g of toluene was added, the mixture was heated until a reflux state, and water was collected by a Dean-Stark apparatus. 25.0 g (0.104 mol) of 3-chloropropyltriethoxysilane, 3.1 g (0.021 mol) of sodium iodide, and 100 g of N-methyl-2-pyrrolidone were further added, and the mixture was stirred under heating for 3 hours while the solvent was distilled off at 150° C. The reaction liquid was separated using toluene and water, activated carbon was added to the organic phase, the organic phase was stirred and filtered, and toluene was removed by an evaporator, to obtain a crude product. The crude product was distilled under reduced pressure, to obtain a compound 1 as a target at a ...

example 2

Production of Compound 2

[0065]

[0066]38.1 g (0.156 mol) of 4-trifluoromethylbenzene-1-sulfonyl chloride, 19.6 g (0.156 mol) of sodium sulfite, 39.3 g (0.467 mol) of sodium bicarbonate, and 100 g of water were placed in a 500-mL recovery flask, and heated to 100° C., and a reaction was caused for 1 hour. Subsequently, 100 g of toluene was added, the mixture was heated until a reflux state, and water was collected by a Dean-Stark apparatus. 25.0 g (0.104 mol) of 3-chloropropyltriethoxysilane, 3.1 g (0.021 mol) of sodium iodide, and 100 g of N-methyl-2-pyrrolidone were further added, and the mixture was stirred under heating for 3 hours while the solvent was distilled off at 150° C. The reaction liquid was separated using toluene and water, activated carbon was added to the organic phase, the organic phase was stirred and filtered, and toluene was removed by an evaporator, to obtain a crude product. The crude product was distilled under reduced pressure, to obtain a compound 2 as a targ...

example 3

Production of Compound 3

[0068]

[0069]24.25 g (0.125 mol) of 4-fluorobenzene-l-sulfonyl chloride, 15.7 g (0.125 mol) of sodium sulfite, 31.4 g (0.374 mol) of sodium bicarbonate, and 100 g of water were placed in a 500-mL recovery flask, and heated to 100° C., and a reaction was caused for 1 hour. Subsequently, 100 g of toluene was added, the mixture was heated until a reflux state, and water was collected by a Dean-Stark apparatus. 20.0 g (0.083 mol) of 3-chloropropyltriethoxysilane, 2.5 g (0.017 mol) of sodium iodide, and 100 g of N-methyl-2-pyrrolidone were further added, and the mixture was stirred under heating for 3 hours while the solvent was distilled off at 150° C. The reaction liquid was separated using toluene and water, activated carbon was added to the organic phase, the organic phase was stirred and filtered, and toluene was removed by an evaporator, to obtain a crude product. The crude product was distilled under reduced pressure, to obtain a compound 3 as a target at a ...

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Abstract

A method of producing a silane compound having a Formula (1) sulfonyl bond includes reacting a Formula (I) chlorosulfonyl compound with sodium sulfite in water as a solvent in the presence of a base, to produce a Formula (II) sulfinic acid sodium salt: and adding an aromatic hydrocarbon solvent to carry out azeotropic dehydration, and adding an aprotic polar solvent and a Formula (III) chloroalkylsilane compound.(wherein R1, R2, R3, R4, and R5 are each independently a substituent selected from a hydrogen atom, halogen atom, alkyl group, alkoxy group, haloalkyl group, haloalkoxy group, cyano group, and nitro group, R2 and R1 or R3 may form —CH═CH—CH═CH —together, R6 and R7 are each independently a C1-5 alkyl group, L is a single bond or saturated or unsaturated divalent C1-19 hydrocarbon group having a linear, branched, cyclic structure, or a combination thereof, and q is an integer of 1 to 3).

Description

TECHNICAL FIELD[0001]The present invention relates to a novel method for producing a silane compound having a sulfonyl bond useful for a raw material for a composition for forming an underlayer film between a substrate and a resist (such as a photoresist, an electron beam resist, and an EUV resist) used in production of a semiconductor device.BACKGROUND ART[0002]Fine processing by lithography using a photoresist has been conventionally carried out in production of a semiconductor device. The fine processing is a processing method in which a thin film of the photoresist is formed on a semiconductor substrate such as a silicon wafer, irradiated with an active light such as ultraviolet light through a mask pattern that has a pattern of the semiconductor device, and developed, and the substrate is etched using the obtained photoresist pattern as a protective film to form fine concaves and convexes corresponding to the pattern on a surface of the substrate. In recent years, an increase i...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): C07F7/04C07F7/18
CPCC07F7/1892C07F7/1804C07F7/1872
Inventor TAKASE, KENJI
Owner NISSAN CHEM IND LTD
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